Ashley's Dilemma
by doneandmoredone
Summary: Ash decides that he enjoys dressing up like a woman, so does.  Gary bumps into a "stranger" by the name of Ashley in Pallet Town one day and falls for 'her.'  Oh the awkward.


**Title:** Ashley's Dilemma

**Author:** Risa

**Pairing:** Gary/Ash(ley)

**Rated:** K+

**Disclaimer:** Pokemon is not mine.

**Word Count:** ~4,000

**Summary:** Ash decides that he enjoys dressing up like a woman, so does. Gary bumps into a "stranger" by the name of Ashley in Pallet Town one day and falls for 'her.' Oh the awkward.

**Warning:** In case the title and the summary didn't make this completely obvious, this fic contains crossdressing and homosexuality. You have been warned. What you read and get offended by from here on out is not my problem.

**A/N:** This is obviously set in the anime, but reader beware. I didn't watch most of it, so my knowledge is flawed and I may have missed crucial pieces of character-development. Treat this as an AR, where it sticks with canon through the Indigo League and deviates from there. This fic's based on and inspired by one of the early episodes anyway.

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><p>It occurred to Ash one day that he had become dreadfully bored with his life as Ash Ketchum. No matter how many times he set out on a new adventure, he was nowhere close to becoming the very best like no one ever was. He had many traveling companions in his day, as well as many pokemon, though he was forced to say goodbye to almost all of them for one reason or another. Most of them had their own paths to follow which deviated from Ash's, and where goodbye was no longer unusual to him, he just didn't have the will or the energy to do it again as he was.<p>

Something in his life wasn't quite working. All of the battles and all of the trials he had faced with his team all meant something, though it had become embarrassing to start at square one no matter where he set off to. It was as though his passion for pokemon wasn't quite there, but that certainly couldn't be the case. No, the problem wasn't with pokemon, but with the fact that he didn't quite feel like himself no matter where he went, or what he did. There was a hole that his pokemon journeys just couldn't fill.

The thing is, he knew exactly what this hole was, but spent years denying it. After all, it was something that simply wouldn't be expected of him, and if he was going to be a pokemon master he simply had to keep a good image. It took him about eight years to realize that he wasn't going to accomplish anything by denying himself the permission he needed to be exactly who he wanted to be.

That's when he began to raid his mother's closet in secrecy. He had Pikachu distract Mr. Mime on days when he tried on his mother's dresses. The desire to wear women's clothes hit him sometime just before his early teens. He found that the few times he wound up crossdressing for one reason or another weren't so bad. For example, when Team Rocket helped him infiltrate Erika's gym because he was completely determined to get that badge at any cost. He still hated gross things like perfume and make up, even to this day, and still couldn't quite understand why anyone would wear high heels.

The dresses were a different story, though. He couldn't help but remember how comfortable it felt. Well, not the people staring at him suspiciously, but the dress itself. It just felt cool around the knees, and he was the slightest bit determined to twirl in it just once, though that was really weird, and only creepy people like James did that. At least, that's what he thought at the time.

He dismissed those desires every time they popped up, and even was able to drown them out and forget all about them on his various journeys.

The older he got, though, the more he reveled at the thought of putting on dresses. He didn't like wigs so much at first because some of them were really itchy, but he managed to find a nice blonde wig similar to the "Ashley" one he had that caused him no problems. It was a whole new world, sporting that wig, trying on his mom's clothes. Strange thing about her wardrobe, some dresses were snug like a glove, and others didn't fit quite as well, particularly around the shoulders. It was weird, but it was almost like she bought some of them with him in mind, though that couldn't possibly be. His mom loved him, but even she had to have limits. How would she feel if she saw her son like this?

One day, though, he decided that she simply had to know. Her son was just as much a crossdresser as he was a destined pokemon master. She would accept him. He knew she would.

He hoped she would.

So she came home one day to find her son sipping tea at her kitchen table with Pikachu and Mr. Mime. Ash half expected her to tell this strange girl to leave her house, or to ask if this strange girl was a friend of her son's. He thought the dress and the wig were enough to obscure his identity. After all, he became a whole new person in front of the mirror. Or she would recognize that the dress was hers and chastise him for raiding her closet.

Of course, his mother had a knack for saying what he least expected. "You look lovely, dear. Now help Mimey put away the groceries."

His jaw hit the table, yet never loved his mom more in his life. As soon as she put the grocery bags on the table he pulled her into a great big hug and told her "thank you." Now she was the one who was confused. After all, who thanks their mother after being assigned chores?

Over dinner, his mother asked him which style of dress he preferred, as well as which colors. Did he wear nylons? Also, he needed some cute shoes to go with. It was really embarrassing at first. A side of himself that he denied especially to himself for years had finally reared itself, and his mother treated it as though it were no big deal. In fact, she seemed to be enjoying this way too much.

He begged her not to tell anyone. Also, he expressed desire to travel the world as "Ashley" for awhile, just to see if that would help him on his journey. She thought it was a wonderful idea, and set off right after dinner to do some shopping. After all, he needed to get started on his whole new wardrobe.

The very next day he was packed and ready to go, the locks of his favorite blonde wig spilling over the long-sleeved baby blue dress his mother picked out for him. It had a high collar to hide his lack of cleavage, and it came with a yellow scarf to hide his adam's apple. The skirt of the dress billowed out just below his knees, and he had on white knee-high socks and a pair of comfortable black flats. He still had to wonder if his mom had known that this would happen all along and prepared for this day. After all, she was full of surprises.

"I'm gonna miss you, sweetie," she said, giving "Ashley" one last kiss on the cheek before he took off. Ashley made a very convincing girl. After all, he didn't have to shave much, he was kind of tall for a girl, being half a head taller than his mom, who was the average height for a woman. Still, Ashley was short for a boy. He still had facial features androgynous enough that the dress and the wig really sold the image. His face was still round-ish, his eyes were wide and full of life, with long eyelashes and pink cheeks to complete the image. He would finally be a whole new person, setting off on a real new journey once and for all.

The only thing that could possibly give him away was the pikachu riding on his shoulder, but some things simply couldn't change. His journey would be incomplete without his best friend, and the whole purpose was of this new journey and this new persona was completion.

He would be the best trainer the world had ever known, and do it just the way he was. He would do it as a man in women's clothing, and if the world didn't like that then they would simply have to deal with it.

The hardest part was figuring out which region to tackle first. There was hardly a corner of the world left untouched by Ash Ketchum anymore, so he figured it would be a good idea to revisit a region that stood out most to him back in his day. Johto, Hoenn, Sinnoh, and Unova all came to mind, though it was a tough choice. He didn't want to risk going through Kanto's Pokemon League, seeing as he was most well-known in this region, and he just wasn't ready to be spotted yet. With that in mind, he figured Johto would also be a bad idea, but if he started talking himself out of that one then he would start talking himself out of the others and come crawling back home. He pinched his eyes shut and shook his head. No, he absolutely had to stay strong.

In the whopping two seconds that his vision was obscured, he bumped into someone just hard enough to take him completely by surprise and knock him backwards. It was way too early in the morning for anyone to be out, yet he had managed to run into the one person who was.

Of all the people in Pallet Town to come across first, he had to run into Gary Freakin' Oak of all people. "Ah!" he said in his normal voice, though he quickly covered that up by clearing his throat and cranking his voice up a few notches in the most feminine voice he could conjure. "I mean oh, oh! Excuse me."

"No, excuse me," said Gary, extending his hand to the fallen lady. Ash didn't know that Gary of all people was capable of taking up such a polite tone, and in all honesty it was kind of gross to hear. He reluctantly took the hand of his former rival and allowed himself to be pulled up. That hand felt way too hot against his own, and it lingered there just a tad too long for his comfort.

Ashley blushed and bowed, more to hide 'her' face than anything. It didn't seem that Gary recognized him and he wanted to keep it that way. Of all the people who could potentially exploit and completely ruin him, it was Gary. Granted the other boy had cooled it with his jerk-like tendencies throughout the years, Ash didn't think for a moment that this of all things would fly. Besides, the only person who knew his embarrassing secret was his mom, and he intended to keep it that way for the time being.

"Have we met?" Gary asked, trying to get a good look at Ashley's face. 'She' jerked 'her' head back up and flailed 'her' hands back and forth whilst giggling nervously.

"No, no. Nope. I wasn't born here. In fact, I've never been here before in my entire life. Just passing through, and I simply must be going."

"Wait a minute," said Gary, placing his hand on Ashley's shoulder. "Won't you at least tell me your name?" This was beginning to boarder on sexual harassment. He could use that as ammo to break loose, but that was kind of a stretch, and he really didn't want to stand out, or draw any attention toward himself. Ash could not reveal himself, especially not to Gary of all people. He had to keep his cool no matter what.

"Ashley. My name is Ashley."

Gary's eyes twinkled, and he smiled. "That's a pretty name."

Ash blushed again, and his stomach started to churn. Gary Oak was... flirting with him. It was the single most awkward and unnerving thing that had ever happened to him in his entire life. He hadn't considered how he would deal with any guys that happened to fall for him, though considering how often he'd traveled with Brock he really should have. In fact, Brock hitting on him is perhaps the only situation that could possibly be worse than this one, though he wasn't sure if his disguise was quite that convincing. It seemed to fool Gary, though.

Without saying a word, Ash tried to back out of Gary's touch, only to have that arm of his weave around 'her' shoulders. The shoulders were broad, more so than the hips of course, though the dress did a good job of hiding that. Not that Gary was complaining. He seemed perfectly content to walk back through town just like that, pointing out places in Pallet Town that Ash very much knew about, but Ashley was new to Pallet Town, as well as the rest of the world. 'She' got an earful about Gary's life, and everything he was working on. He expressed a strong desire to get out there and start challenging leagues again, believing that he was finally strong and mature enough to be worthy. It was exciting news, really. Ash had always considered Gary to be his greatest rival.

Even so, he said nothing, just allowing Gary to say whatever it was he needed to. Whenever an opportunity to get away presented itself Ash would be right on it, though his rival was relentless. He even went as far as to ask Ashley all about 'herself,' such as where 'she' was from, what 'her' hobbies were, what 'her' dreams were, and so forth. 'She' was a trainer from the Sinnoh region who dreamed of becoming a pokemon master. 'Her' hobby was fashion. 'Her' pikachu was her partner through and through. Gary mentioned that he had a friend from right here in Pallet Town that walked around with a pikachu on his shoulder, too, and what a strange coincidence that was.

By the time that conversation came up, Ash's stomach growled. He giggled nervously when Gary stared wide-eyed at her stomach. He offered to treat Ashley to lunch, which was an offer that 'she' wasn't exactly inclined to refuse, despite the circumstances. After all, Ash did think better with a full stomach.

He also thought that, as long as Gary had him in his clutches, he might as well take advantage of it. While they were out to eat, Ashley asked Gary, "What is this Ash fellow you keep mentioning like? He sounds like a real-" Quickly, thought Ash, what words would a girl use? A girl that wasn't Misty, May, or Dawn anyway, "-sweetie?"

"Pffft!" Gary snorted, then broke into full-blown laughter. Ashley had to refrain from throwing the french fries Gary had bought for 'her' at him. Once a jerk, always a jerk.

"What's so funny?" Ashley said through barred teeth.

"You're really cute, Ashley. You know that?"

"I-" was on a date with Gary Oak and failed to realize it until that very moment. "I have to go."

Before 'she' could get up, Gary placed his hands upon 'hers' and gazed into 'her' eyes intently. Suddenly his chest raced like a rapidash, and blazed like one's mane. All this time Ash had been avoiding eye contact, hoping it would help keep his identity secret, and perhaps even hint toward not being interested in Gary, because he wasn't, though his words and actions seemed to suggest otherwise. Still, just because Ash dressed like a girl didn't mean he wanted a... a boyfriend. That was just a stigma that came attached to what he did. All he wanted was to be his real self and to become a pokemon master. There was no time for romance, least of all with Gary.

"That's a shame. We were just getting to know each other. Are you sure?"

"Well-" yes. Yes. YES. It shouldn't have been hard, but Gary was both unrelenting and very persuasive. It certainly explained why he once had his own car and cheerleaders back in the day. He could be a real douche, but he definitely had charisma, and he was apparently difficult to refuse, even in a situation like this. Perhaps, Ash thought, he could throw Gary off by pretending 'she' was more interested in another man than him.

So Ashley gave her most charming smile, and returned to the previous subject. "So about that Ash friend of yours. Surely he isn't that bad?"

Gary's face dropped into a real serious grimace for a second. He then removed his hands from hers and crossed his arms. What was that look for? Since when had he himself become a touchy subject? Or did Gary suspect something? Shit.

"Why do you keep asking? You know him or something?"

"No! Well, sort of," said Ashley, clutching her now cold fries. A nervous habit of his was to eat whenever his mouth was working faster than his brain, but if he brought those fries to his mouth it was possible that he'd give himself away. Gary knew him very well, after all. Instead, he offered to let Pikachu pick at them, though his pokemon was busy licking ketchup from a bottle like it always did. At least Gary didn't know his pikachu's mundane little habits as well as Ash's. Still, this little date of sorts went on too long and it needed to end, though try as Ashley might Gary just wouldn't let 'her' go.

"Read about him in some magazine? Caught him on the tube? The renowned champ of all regions.

"What a joke! He's nothing but a stupid loser, you know. He's whiney, sensitive, slow as slowpoke. I've known him pretty much since I was born, so you can take it from me. He's not worth your time."

Ash had to conjure every ounce of strength not to lash out at his former rival. After all, no one was being more whiney, sensitive, and slow as slowpoke as Gary was at that moment. Still, was this the way he spoke of Ash to all strangers? Of all the nerve. He deserved to have that plate of mushed french fries smashed into his face. It hurt that Gary still spoke of him this way. Was anything he did ever going to be good enough?

"Actually, I was on my way to see him. Gramps said he came back, though he didn't even bother to stop by and say hi. He's probably long gone by now anyway, off to restart his pokemon journey from square one like he always does.

"Though to tell the truth, I'm the real loser here."

Ash was taken aback by that admission. It was exactly what he was thinking, yet to hear Gary himself say it swept his mind clean of all meaningful thought. He just had to ask, "why do you say that?"

"Eh? Forget it. It's stupid. You want to go?"

Ashley nodded, and the two of them headed back outside. For the longest time they exchanged no words, and the tension in the air was as heavy as a snorlax. Clearly Gary was in a bad mood, and now Ash was in the rather peculiar position of wanting to ditch him and cheer him up at the same time. He was still mad about all those things Gary said about him, but it was pretty obvious why Gary said all of those things. He was jealous. Ash proved to be a better trainer than him, and he was still driven to improve, even now. Gary couldn't keep up, but it seemed like he wasn't really trying to. Ash always thought his former rival had things in his life all figured out, that he was on top of everything, yet something was off. Something weighed on his mind.

Before Ash could even begin to try to figure any of it out, they had reached the end of Pallet Town. He thought that this was where they'd part, but Gary just kept going. Not only did they keep going, but he laced his fingers through 'hers' and heaved a sigh.

"I know we've just met, but I feel like I've known you my whole life. Isn't that strange?"

Ashley gulped, hoping with every fiber of 'her' being that this wasn't going in the direction that 'she' thought it was. After all, they had only just met, 'her' and Gary. Ash Ketchum was just some "stupid loser" he actually did know all of his life. What would happen if Gary found out that they were the same person?

"Would you mind if I kissed you before you got going?"

Shit. Think. What would a girl do in this sort of situation? It depended. Was this supposed to be creepy, or romantic? Oh, he had already established that using the girls he knew as a frame of reference was a bad idea, but he had nothing else to go by. He wasn't a girl. He dressed like one and regretted nothing, even though he wound up in the most awkward situation ever because of it. He couldn't exactly let Gary kiss him, could he? If he did that then what was stopping other guys? What if he ran into Brock? The thought shook him to the core.

"I don't think that's such a good idea. I mean, it's not like we'll ever see each other again."

"I wouldn't be too sure," said Gary. "It's not like you've gotten rid of me before, but you sure tried."

Ash felt sorry for him. He liked Ashley so much, and 'she' spent the entire time trying to get away from him. This was an identity he hoped to wear with pride someday, yet he was so determined to get away from Gary that he considered kissing him just to get away. If he kissed Gary as he was then he could never be who he truly wanted to be without betraying his former rival and friend. If he reveled who he was to Gary then he would leave Pallet Town feeling what? Embarrassed? Ashamed? That hardly seemed fair. Either way Gary would probably be upset, though it seemed honesty was the best route to go now.

"That's because... I'm not who you think I am, OK?"

Gary's face hovered just inches above hers, and she could feel his breath sweep across her face.

"I know exactly who you are, loser."

He ran his fingers along the back brim of her wig and closed the gap between them, in the most hot, heartfelt, honest (not to mention only) kiss Ash had ever gotten. He almost wanted to cry. How was he supposed to know that Gary had a thing for him? More importantly, he couldn't quite figure out how he himself felt about it. He never had time for a girlfriend, so he just never really did much with girls. Gary made him feel all kinds of things, most of which he wasn't even aware of until today, and his former rival broke their kiss he found himself wanting another. It was the weirdest thing.

"Now get lost, Ashley. I know you have things to do. Just keep in touch or something, would ya?"

Not only his mom, but now Gary, too. He expected to be mocked, belittled, and, well, he was, but only for all of the usual reasons. Where it counted, Gary understood. He understood completely.

So Ash couldn't resist throwing his arms around Gary, though he couldn't find the words to say. He just reveled in being accepted for who and how he was.

END


End file.
